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I’m enviously sneaking looks at the guy sitting next to me. It’s pretty obvious that he’s a winner.

LOS ANGELES, CA - JUNE 18: The Microsoft tablet Surface is unveiled during a news conference at Milk Studios on June 18, 2012 in Los Angeles, California. The new Surface tablet utilizes a 10.6 inch screen with a cover that contains a full multitouch keyboard. (Image credit: Getty Images via @daylife)

We’re on a four-hour flight to Denver on a WiFi equipped plane and he’s got an iPad. I’m watching him. He’s thoroughly enjoying it. I can see he’s using it to read the New York Times. And he’s checking email and browsing the web. An hour or so into the flight he’s absorbed in an episode of Homeland. I notice that the screen resolution is...well...brilliant. I also notice others on the plane with their iPads – watching videos, listening to music and reading. As we prepare to land, my seatmate neatly tucks the little device away into his shoulder bag like it was a paperback book. Like the other iPad users, he’s a winner. He’s happy and cool and probably connecting on a flight back to the Bay area where he’ll sip California wine and discuss that week’s zillion dollar deals with his venture capital friends (who will also be using iPads).

Me? I’m hunched over my little HP 3105m sub-laptop running Windows 7 Home Premium. What a loser I am. I’m not reading The New York Times on it. I’m not listening to music. And even with 8GB of RAM stuffed into it, I’m not doing much surfing.

But you know what? I like the little guy. I travel a lot and this is my companion. It’s only three-and-a-half pounds and has an 11.6” screen. The specs say its battery will go more than nine hours, but I’m usually getting about six out of it, which is fine for most of my trips. I look around and see a few other guys like me, hunched over their laptops, feverishly typing out proposals or working on spreadsheets. They’re not playing either. They’re working. And unlike my seatmate they look harassed and stressed. They’re not going to the Bay area. They’re heading back to their cubicle somewhere in the Northglenn industrial park to run more numbers and then maybe drink a case of Rolling Rock while watching the Broncos play next Sunday.

Microsoft wants to change this situation. This week. Because this week they’re introducing their answer to the iPad, called the Surface. It’s targeted at guys like me: the working business user. You know...losers.

Sure, we like our entertainment. We like to read books and magazines on our devices. We like to watch movies and surf the web. But we also need to do some real work. And not just checking our stock prices or tapping out an answer to an email or two. We need a device that we can use to create documents and spreadsheets and presentations. We need something that can be used to remote into our office systems and enter orders and update customer information. We need to work online, in the cloud, but also offline and locally too. And we’re still mostly using Microsoft software. We need a device that’s Microsoft friendly. So this week we get the Surface. Will businesses buy this device? Will I? Will the Surface turn me into a winner?

I have to admit, it’s tempting. I’ve got no reason to replace my HP laptop at this moment but I do have a few complaints. The screen is small and the performance, particularly when going online, is sometimes slower than I’d like. I could never hope to watch a movie on it nor have I ever considered it as an e-reader, mainly because I’m more than happy with my Kindle. And no matter how much tweaking I do, the touchpad remains oversensitive to my slow-moving fingers. But I’m mainly using it as a portal to my office, remote desk-topping in and writing, reviewing and writing and reviewing. And it works pretty well. I have Microsoft Office 2010 installed on it and that works fine too. And it’s light. It has 3 USB ports which I use a lot and it even has a display port which I use all the time when doing presentations.

But I want to be cool like my Denver-bound seatmate. Should I make the leap and get a Surface? Why don’t I just get an Ultrabook laptop? Or an iPad?

For starters, an iPad is out. As I mentioned before I do a lot of typing and other office work on my laptop. I can’t do this on a small tablet screen and I don’t want to drag around a keyboard accessory. I need to store some files and presentations locally and need to work offline and there isn’t a version of Microsoft Office for the iPad. Yes I know that many people are happy with their add-on keyboards and there are plenty of Office knock-offs available for the iPad. I’m sure I’m being too stubborn and inflexible. But at my heart I’m a Microsoft guy. My company sells Microsoft products. So for me, it’s really a decision between the Microsoft Surface and an Ultrabook laptop.

The price is going to be about the same. I’d likely wait to buy the Windows 8 Pro model of the Surface which will support the latest Office version and have the USB 3.0 port which I know I’ll use. That device, once I buy an additional power supply (I tend to lose those) and the inevitable adaptor for a projector and other USB add-ons, will easily set me back a grand I’m sure. An Ultrabook, like the highly rated Toshiba Portege, will cost around the same. I’ll keep my fingers crossed that my purchase certificate is still intact so I’m allowed to install my already-purchased version of Office on either device without displeasing the Microsoft licensing Gods.

The Toshiba Portege Ultrabook that I’m looking at would be about a pound heavier than a Surface (but a pound lighter than my current laptop). And it would (at least for now) not have a touchscreen, which I really don’t need. Like the Surface it would run Windows 8. I’m not sure about the browsing experience. But I am sure of this: it would have three USB ports (including USB 3.0), a full sized keyboard, a display port and a 13.3” screen, which is a relief to my poor, tired eyes. It has a built in webcam (I Skype a lot) and will run for about 7 hours under my typical use which is a little longer than current laptop would last.

If I were a retail shop I’d be tossing my cash registers and equipping everyone with tablets. If I were running a landscaping business I’d give my crew chiefs a tablet to key in work-orders at the end of the day. If I had a warehouse I’d have my employees use a tablet for bar coding and inventory management. If I managed a team of salespeople who were visiting prospects and filling out call reports I’d give them tablets too. And if, like most of my clients, we were running Microsoft applications, or may want to hire a Microsoft developer to create something, or have a Microsoft infrastructure with Microsoft security and Microsoft partners supporting my business I’d likely cut down on the chance of any incompatibility headaches and just buy the Microsoft Surface. Apple enthusiasts may vomit at this, but from a business perspective, it seems like a reasonable direction to take.

But as for me? The travelling business owner with the tired eyes and the arthritic fingers who needs a productive work tool all the time? Unfortunately...no, the Surface is not going to work for me. Look - I really wanted to finally buy a tablet because I want to have fun and be a winner like the guy sitting next to me on my flight to Denver. But rationale has taken over. I’m forced to remain in the laptop world. I will likely buy the Ultrabook. A tablet, even a Microsoft tablet, may be fun. But it’s just too....small and unproductive for a loser like me.